The Dinner Questions That Actually Make People Interesting
Some of my favorite conversations have started with these questions. I hope they spark a little magic at your table, too.
Some of the best conversations I’ve ever had started with a completely ridiculous question.
via Pinterest
Not “What do you do?” or “Where are you from?” but things like:
What’s the most irrational hill you’ll die on?
If your life had DVD bonus features, what would they include?
There’s something oddly magical about asking people questions they weren’t expecting. The walls come down. People laugh. They tell stories they’ve never told before. Sometimes you learn more about someone in ten minutes than you would’ve after months of small talk.
I’ve been collecting conversation starters for years. This list has made appearances at birthday dinners, while traveling, first hangs, first dates, and at conferences with people I barely knew. It has never failed me. And shoutout to some of my friends for adding some of these to the list!
So the next time you’re sitting around a table or something and someone says, “So… what should we talk about?” — pull out this list!
You never know which question will become the story you laugh about years from now.
Let’s get into it…
What do you want etched on your tombstone?
If you had to cook a dish to impress Gordon Ramsey, what would it be?
What musical artist do you think is overrated?
What part of a hamburger would you be?
What was your last Google search?
What fun fact do you always use in Never Have I Ever or Two Truths and a Lie?
What role did you play in group projects at school?
What’s the perfect temperature?
Do you kill spiders or let them outside?
When you read, do you hear a voice in your head? Do you have an inner monologue? Is it your voice or someone else’s?
Have you experienced anything paranormal?
Do you have any superstitions?
If you came with a warning label, what would it be?
What type of plant would you be?
What is the most obscure thing that you hate?
Small dog person or big dog person?
What do you wish you didn’t judge people for, but you do anyway?
What assigned book in school had an impact on you?
What’s your go-to comfort show or movie?
If you could have anyone narrate your life, who would it be?
Who is your favorite Hollywood Chris?
Would you rather explore all the ocean or all of space?
What is your favorite conspiracy theory?
How old are you in your head?
What type of noodle would you be?
What type of fish would you be?
What time of day are you?
In the event of an apocalypse, are you staying and fighting or giving up?
Do you have different cups for different drinks?
Is water wet?
Did you fail any classes in school?
What color is your favorite song?
If your life had DVD bonus features, what would they include?
Are you a dessert or an appetizer person?
If you could be any celebrity’s sibling, who would you pick?
If you could take out any body part and give it a rinse, what would it be?
If your pet had a voice, what would it sound like? What celebrity would it sound like?
What’s your go-to hangover meal?
What do you daydream about before you fall asleep?
Do you believe everything is a coincidence or do you believe in fate?
If you had to pick a fantasyland to live in, where would you live?
If you had to listen to the same song every morning when you wake up, what song would you choose?
What movie or show do you wish you could watch again for the first time?
Do you return your shopping cart?
Men who should be allowed to live if women take over the world (sorry, men)
Do you have any actual phobias?
What’s your go-to dance move?
What’s something you beleive in that you think other people would judge you for?
What’s a niche red flag that immediately turns you off?
What’s a topic you could give a presentation on without any prep?
What was the last thing you did for the first time?
What is a fictional bar/restaurant/cafe you want to visit in real life?
Did you color code your classes in school?
What’s the most irrational hill you’ll die on?
What would your blood and body be? (Like Jesus)
What scents remind you of home?
What do you believe is the most quintessential pop song?
What type of wild animal do you wish you could have as a pet?
Which mythical creature are you glad doesn’t exist?
What food do you judge other people for liking?
What was your favorite Vine?
If you were a ghost, what building would you haunt?
If everyone in the world stopped sneezing, how long would it take for you to notice?
Do you wish we could have just one season or all four?
Have you ever experienced crazy deja vu?
What’s something about you that you wish everyone already knew about you, without having to tell or explain it to them?
If you could have any mythical creature as a pet, which would you choose?
If you had a box full of all the things you’ve ever lost, what would you dig for first?
What is a mystery in your life you wish you had the answer to?
If you could have a full-time staff member, what would they do?
What is something you love that you wouldn’t recommend to others?
What’s a lesson you keep re-learning?
What’s a piece of advice you give others, but struggle to abide by?
What’s a small moment from your life that seemed insignificant at the time, but you think back on a lot?
What’s a piece of common advice you disagree with?
What’s something that’s far-fetched that you think will be common sense/knowledge in 25 years?
What are arbitrary rules you have for yourself? (i.e., I don’t initiate plans with someone more than twice if they always say no/cancel/never initiate with me)
If you could be an expert in one subject, what would it be?
Do you think the goal of traveling is to visit as many places as possible, or to find a place you love and keep going back to?
Do you believe in Karma? And is there any crazy thing that happened that made you believe in Karma?
If you had died, what 5 items would your friends need to use to conjure you?
What thing/trend/practice from the past do you think we should bring back?
What’s something you were on the wrong side of history on?
What stereotypes do you think are true?
What’s something you’re weirdly good at that has absolutely no practical value?
If you didn’t have to worry about money, what would you do for work?
What opinions do you have that seem the most out of line with your general political affiliations?
Who would play you (and all the important people in your life) in a movie about your life?
Have you ever told a lie that kept/keeps you up at night?
What is the number one thing on your bucket list?
When was the last time you fell? And did you get up immediately, or how did the embarrassment play out?
Piggybacking off of that last one, what was your most embarrassing moment?
Do you have any weird food combos?
If your life had a DVD commentary track, who would you want narrating it?
What’s the most “this could only happen to me” story you have?
If someone made a documentary about your life, what would the title be?
What’s something you judged people for until you became one of those people?
What’s the most unforgettable compliment you’ve ever received?
What’s a purchase under $50 that dramatically changed your life?
What fictional world do you think you’d actually survive in? Which one would you want to live in?
What’s the funniest thing you believed as a child?
What’s something that instantly tells you, “I’m going to like this person”?
What’s a story your friends are tired of hearing you tell?
What tiny moment in your life felt way more cinematic than it had any right to?
If you could relive one meal - not because of the food, but because of the people and the conversation - which would you choose? (And what did you eat?)
If you end up using any of these, I have just one simple request:
Put your phone down (after pulling up this list, of course), ask the question, and just be surprised by everyone’s answers.
The best conversations aren’t perfectly planned out in our heads — they’re built unexpectedly.
And if one of these prompts leads to an unforgettable story, a new friendship, or a laugh-until-you-can’t-breathe moment… I’d call that pretty solid proof of magic.
Which question was your favorite? Tell me in the comments — or better yet, tell me the funniest answer someone gave!
This post was originally published on my Substack, Proof of Magic.